Educated at Auckland Grammar School, Gillespie made 1,208 runs from his thirty first-class matches at 23.23,[2][3] including one century – 183 against Canterbury in January 1930.[4] He also made six half-centuries, and took two wickets for 35.50 with his occasional bowling.[2] He toured Australia with the New Zealand team in 1925-26 but played in only one of the four first-class matches.[5]
He captained Eden Cricket Club in Auckland for some years; in 1924–25 he shared a 441-run opening partnership with Jackie Mills for Eden against University.[1] He was also an avid rugby player.
^Wisden's obituary refers to him as Hector Donald Gillespie,[1] While both CricInfo and CricketArchive list him as Hector David Gillespie, the Registrar-General's online website has Hector Donald Gillespie for his birth (27 May 1901) and death.[2][3]